Utilization of an aromatic aldehyde 4-methyl-2-hydroxy-benzaldehyde as flavoring ingredient

ABSTRACT

4-Methyl-2-hydroxy-benzaldehyde possesses valuable organoleptic properties and consequently can be used as flavoring ingredient in foodstuffs and beverages as well as in tobacco.

BRIEF SUMMARY OF THE INVENTION

The instant invention relates to the field of flavors, more particularlyit provides a process to enhance, modify or improve the flavorproperties of foodstuffs, beverages, smoking tobacco and tobaccoproducts, which process comprises the step of adding thereto a small butflavor effective amount of 4-methyl-2-hydroxy-benzaldehyde.

This invention provides also a flavoring composition which contains as aflavor active ingredient 4-methyl-2-hydroxy-benzaldehyde.

BACKGROUND OF THE INVENTION

4-Methyl-2-hydroxy-benzaldehyde is a known chemical entity [see e.g.:Ber. 11, 773 (1878) and Bull. Soc. Chim. France 35, 129-134 (1924)],sofar however, its organoleptic properties have remained unrecognized.

Though, it represents a simple higher homolog of prior used salicylicaldehyde, the compound of the present invention possesses unexpectedlyan original flavor character which is distinct from that shown by thislatter compound. In fact, salicylic aldehyde possesses a spicy andirritating odor similar to that shown by compounds such as benzaldehyde,acetophenone or nitrobenzene, accompanied by a marked phenolic notewhich renders its utilization rather difficult. In contradistinctiontherefrom, 4-methyl-2-hydroxy-benzaldehyde develops a sweet gustativenote of caramel and burnt type reminiscent of some of the aspects ofcoumarin.

Preferred Embodiments of the Invention

Owing to its organoleptic properties, 4-methyl-2-hydroxy-benzaldehydecan find a wide range of utilizations either in the direct aromizationof foodstuffs, beverages and tobacco, or in the manufacture of flavorcompositions of various nature.

Its intrinsic characters match well with those of most of the commonlyencountered flavor ingredients and it can enter in the manufacture ofcompositions of caramel, vanilla, cocoa, chocolate, nut, hay, tobacco orcinnamon type, or it can be used as partial substitute for coumarin.These compositions are particularly suitable for the aromatization offoodstuffs in general, especially of bakery and confectionary products,and of beverages, viz. those of milk and cocoa base, of yoghurts and oftobacco of natural and synthetic origin.

The concentrations at which the aldehyde of the invention developsinteresting gustative effects can vary in a wide range of values.Preferably, they are of between about 0.1 and 10 ppm (parts per million)by weight based on the total weight of the flavored material. Of course,these values can be much higher than the above given upper limit,especially whenever 4-methyl-2-hydroxy-benzaldehyde is utilized in themanufacture of aroma concentrates. In the aromatization of tobacco andtobacco products, the typical concentration average value is in theorder of 50 ppm, it can be however of between about 5 and 200 ppm.

As stated above, 4-methyl-2-hydroxy-benzaldehyde can be added directlyto the material to be flavored. Typically however, it is used insolution in common edible solvents such a dipropylene-glycol ortriacetine, or over solid supports, for instance gum arabic or dextrine.

4-Methyl-2-hydroxy-benzaldehyde can be prepared by one of the knownmethods, for example starting from m-cresol according to G. Casiraghi etal., J. Chem. Soc., Perkin I, (1980), 1862-5.

The invention is illustrated in a more detailed manner by the followingexamples.

EXAMPLE 1

A base flavor composition of vanille-caramel type was prepared by mixingthe following ingredients (parts by weight):

    ______________________________________                                        Maltol                  15                                                    Vanillin                200                                                   Ethyl-vanillin          50                                                    Anisic alcohol          10                                                    Acetoine                5                                                     Rhum ether              20                                                    Propylene-glycol        700                                                   Total                   1000                                                  ______________________________________                                    

By using two aliquots of 100 g each of the above compositions, two novelcompositions were prepared as follows:

    ______________________________________                                                         A "control"                                                                            B "test"                                            ______________________________________                                        Base composition   100        100                                             4-Methyl-2-hydroxy-benzaldehyde                                               10% in ethanol     --         20                                              95% Ethanol        900        880                                                                1000       1000                                            ______________________________________                                    

Compositions A and B thus prepared were separately diluted in crystalspring water at 0.1% and subjected to an evaluation by a panel of flavorexperts. Their comments were as follows:

    ______________________________________                                        Composition A:                                                                          vanilla note                                                        Composition B:                                                                          vanilla-caramel note with a slightly coumarinic                               aftertaste.                                                         ______________________________________                                    

EXAMPLE 2

0.5 g of a 1% solution of 4-methyl-2-hydroxy-benzaldehyde in 95% ethanolwere sprayed onto 100 g of a mixture of "american blend" tobacco. Thearomatized tobacco was used to manufacture "test" cigarettes the smokeof which was organoleptically evaluated by comparison with that obtainedby cigarettes containing unflavored tobacco ("control") preliminarytreated with 95% ethanol.

A group of experts found that the smoke of the "test" cigarettespossessed a milder and more pleasant character, associated with acoumarinic note.

What we claim is:
 1. A method to enhance, modify or improve the sweetgustative note of caramel and burnt type reminiscent of coumarin offoodstuffs and beverages which comprises the step of adding thereto fromabout 0.1 to 10 parts per million by weight of4-methyl-2-hydroxy-benzaldehyde based on the total weight of theresulting flavored foodstuffs and beverages.
 2. A foodstuff or abeverage which contains as a flavor active ingredient4-methyl-2-hydroxy-benzaldehyde at a concentration of between about 0.1to 10 parts per million by weight based on the total weight of theresulting flavored foodstuff or beverage, said ingredient possessing asweet gustative note or caramel and burnt type reminiscent of coumarin.